Phenethyl bromide → 3-(4-Cyanophenoxy)-5-phenethyloxy benzoic acid ethyl ester

HRID 1024741Notes

Reaction equation

HRID 1024741 reaction equation
[CH2:1]([O:3][C:4](=[O:21])[C:5]1[CH:10]=[C:9]([OH:11])[CH:8]=[C:7]([O:12][C:13]2[CH:18]=[CH:17][C:16]([C:19]#[N:20])=[CH:15][CH:14]=2)[CH:6]=1)[CH3:2].Br[CH2:23][CH2:24][C:25]1[CH:30]=[CH:29][CH:28]=[CH:27][CH:26]=1>>[CH2:1]([O:3][C:4](=[O:21])[C:5]1[CH:10]=[C:9]([O:11][CH2:23][CH2:24][C:25]2[CH:30]=[CH:29][CH:28]=[CH:27][CH:26]=2)[CH:8]=[C:7]([O:12][C:13]2[CH:18]=[CH:17][C:16]([C:19]#[N:20])=[CH:15][CH:14]=2)[CH:6]=1)[CH3:2]

Participants

3

Reactant 2

HCID 7666Phenethyl bromideHCID 668184083-(4-Cyanophenoxy)-5-hydroxy benzoic acid ethyl ester

Product 1

HCID 668184813-(4-Cyanophenoxy)-5-phenethyloxy benzoic acid ethyl esterYield 69.5%

Procedure

Using 1.0 g (3.53 mmol) of 3-(4-cyano phenoxy)-5-hydroxy benzoic acid ethyl ester and (2-bromo-ethyl)-benzene (0.65 g, 3.53 mmol) and following the procedure of Example 42(b) afforded 0.95 g of the required product. 1H NMR (CDCl3): δ 1.35 (3H, t), 3.1 (2H, t), 4.2 (2H, t), 4.35 (2H, q), 6.78 (1H, t), 7.0 (2H, s), 7.22 (1H, m) 7.32 (5H, m), 7.42 (1H, m), 7.62 (2H, s).

Sources & evidence

ORD record
ord-75c5cbfd5ed148a1a653bf1325d52864
Source dataset
uspto-grants-2014_05
Patent number
US08722930B2

Reaction notes

Loading…